2-methyl-3-phenyl-2H-benzo[e][1,2]thiazine-1,1-dioxide | 18963-33-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 2-methyl-3-phenyl-2H-benzo[e][1,2]thiazine-1,1-dioxide
• 英文别名: 2-Methyl-3-phenyl-1lambda6,2-benzothiazine 1,1-dioxide；2-methyl-3-phenyl-1λ6,2-benzothiazine 1,1-dioxide
• CAS: 18963-33-2
• 化学式: C₁₅H₁₃NO₂S
• 分子量: 271.34
• InChiKey: UFJKFDGGERBXEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-methyl-2-(phenylethynyl)benzenesulfonamide 在 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以90%的产率得到2-methyl-3-phenyl-2H-benzo[e][1,2]thiazine-1,1-dioxide
  参考文献：
  名称：

  One-Pot Sonogashira Coupling–Cyclization toward Regioselective Synthesis of Benzosultams

  摘要：

  A one-pot method for the Sonogashira coupling and cyclization of 2-bromobenzenesulfonamides and terminal alkynes is presented. This method allows access to a variety of substituted benzosultams regioselectively in excellent yields. The reasons for regioselectivity are interpreted through density functional theory (DFT) studies.

  DOI：

  10.1021/acs.joc.5b00274

文献信息

• A Remarkable Accelerating Effect of Ag-Salt on Intramolecular Cyclization of <i>o</i>-(1-Alkynyl)benzenesulfonamides
  作者：Deepak Kumar Barange、T. C. Nishad、N. Kumara Swamy、Venkanna Bandameedi、Dinesh Kumar、Bukkapattanam R. Sreekanth、K. Vyas、Manojit Pal

  DOI：10.1021/jo701470h

  日期：2007.10.1

  Herein, we report transition metal-catalyzed intramolecular cyclization of o-(1-alkynyl)benzenesulfonamides to afford 3-substituted benzothiazines regioselectively via a C-N bond forming reaction and Cu-catalyzed sequential C-N and C-C bond formation leading to the corresponding 3,4-disubstituted derivatives.
• AgNO3 mediated C–N bond forming reaction: synthesis of 3-substituted benzothiazines as potential COX inhibitors
  作者：D. Rambabu、P.V.N.S. Murthy、K.R.S. Prasad、Ajit Kandale、Girdhar Singh Deora、M.V. Basaveswara Rao、Manojit Pal

  DOI：10.1016/j.tetlet.2012.09.102

  日期：2012.11

  AgNO3 facilitated the intramolecular ring closure of o-(1-alkynyl)benzenesulfonamides via a regioselective C-N bond forming reaction leading to the formation of 3-substituted benzothiazine derivatives. A number of compounds were prepared in good yields by using this inexpensive and safe methodology. All the compounds synthesized were evaluated for their cyclooxygenase (COX) inhibiting properties in vitro. A number of compounds that do not contain an enolic hydroxyl group showed selectivities toward COX-2 over COX-1 inhibition. This was further supported by the predictive binding mode of two compounds with COX-1 and -2 proteins through molecular docking studies. (C) 2012 Elsevier Ltd. All rights reserved.
• Ring-chain tautomerism of imine-amine or ketone-carbinol systems obtained by condensation of dilithio-N-substituted carboxamides or sulfonamides with benzonitrile. Synthesis of cyclic products
  作者：Hamao Watanabe、Chung-Ling Mao、I. T. Barnish、Charles R. Hauser

  DOI：10.1021/jo01256a031

  日期：1969.4
• One-Pot Sonogashira Coupling–Cyclization toward Regioselective Synthesis of Benzosultams
  作者：Sudarshan Debnath、Shovan Mondal

  DOI：10.1021/acs.joc.5b00274

  日期：2015.4.17

  A one-pot method for the Sonogashira coupling and cyclization of 2-bromobenzenesulfonamides and terminal alkynes is presented. This method allows access to a variety of substituted benzosultams regioselectively in excellent yields. The reasons for regioselectivity are interpreted through density functional theory (DFT) studies.